Executive Assistant

TurningPoint Healthcare Solutions LLC; Orlando (FL); On-site; USD 65,000 - 100,000; Full time

Job summary

TurningPoint Healthcare Solutions LLC is seeking an Executive Assistant to the CEO to act as a trusted partner, managing the CEO’s calendar, communications, and complex logistics with discretion and proactive judgment.

The role supports the CEO and senior leaders, requiring adaptability, strong writing, and the ability to handle sensitive information, travel coordination, and board interactions, often outside standard hours.

Qualifications

• Five+ years of progressively responsible executive support, including CEO support.
• Mastery of complex calendar management, travel, and board/leadership meeting coordination.
• Advanced proficiency with Microsoft 365 and willingness to learn new tools.
• Outstanding writing, discretion, and ability to prioritize competing demands.
• Interest in and experience with AI tools to improve productivity.

Responsibilities

• Own and optimize the CEO’s calendar and protect time for strategic priorities.
• Coordinate detailed travel, itineraries, contingencies, and expenses.
• Provide secondary executive support to designated senior leaders.
• Draft, edit, and format executive communications and meeting materials.
• Coordinate leadership and board meetings, prep materials, and logistics.
• Design and improve executive scheduling and information management systems.
• Handle sensitive information with discretion and need-to-know access.

Skills

Calendar management

Executive support

Microsoft 365

Writing/editing

AI tools

Education

Bachelor’s degree or equivalent

Tools

Microsoft 365

Job description

The Executive Assistant to the CEO is a highly trusted, proactive partner who enables the Chief Executive Officer and select members of the senior executive team to focus on the organization’s most important priorities. This role exercises independent judgment in managing executive time, communications, information flow, and complex logistics; anticipates needs; and ensures timely, polished execution of commitments. The position provides primary support to the CEO and coordinated, prioritized support to designated senior leaders.

Success requires exceptional discretion, composure, adaptability, service orientation, and the ability to operate effectively amid changing priorities. The role supports board, client, and leadership interactions and may require evening, weekend, or travel-related availability based on business needs.

• Own and continuously optimize the CEO’s complex calendar, protecting time for strategic priorities and exercising judgment to resolve conflicts and competing requests.
• Anticipate needs, prepare the CEO for upcoming decisions and engagements, and identify logistical or communication risks before they become issues.
• Coordinate detailed travel, itineraries, contingencies, expenses, and timely adjustments.
• Provide secondary executive support to specifically designated senior leaders, with CEO priorities taking precedence and capacity escalated promptly.

Executive Communications & Stakeholder Engagement

• Draft, edit, proofread, and format executive correspondence, presentations, briefing materials, and meeting agendas in the appropriate voice and with exceptional accuracy.
• Triage incoming requests and communications using agreed decision rights; route, elevate, and follow up on time-sensitive matters.
• Serve as a professional, responsive liaison with board members, clients, partners, executives, and internal stakeholders; maintain strict confidentiality.

Leadership, Board & Meeting Operations

• Coordinate executive leadership, board, client, and strategic planning meetings, including scheduling, pre-reads, materials, logistics, and follow-up.
• Maintain organized action and decision logs for assigned meetings; track commitments, owners, and deadlines and elevate overdue items appropriately.
• Coordinate leadership offsites and other CEO-sponsored activities in partnership with relevant internal teams.

Operational Excellence & Independent Judgement

• Design and improve repeatable systems for scheduling, meeting preparation, executive information management, and follow-through.
• Handle sensitive personnel, financial, client, and strategic information with sound judgment and need-to-know access.
• Independently resolve routine and complex coordination issues within delegated authority; promptly elevate decisions requiring executive input.

Adapt to urgent changes while maintaining quality, accuracy, professionalism, and clear communication

Requirements

Work Schedule & Availability

This is a full-time, executive-facing role requiring flexibility to respond to time-sensitive business matters outside standard office hours, including occasional evenings and weekends. Availability expectations, escalation protocols, and backup coverage will be established with the CEO. Travel will be required for executive meetings and events.

Required Qualifications

• Five or more years of progressively responsible executive support experience, including substantial support to C-suite executives; CEO support strongly preferred.
• Demonstrated mastery of complex calendar management, executive travel, board or leadership meeting coordination, and high-stakes communications.
• Advanced proficiency with Microsoft 365 (Outlook, Teams, PowerPoint, Word, Excel) and comfort adopting new productivity tools.
• Outstanding writing, attention to detail, discretion, sound judgment, and ability to independently prioritize competing demands.
• AI & Technology Proficiency: Demonstrated interest in and experience leveraging artificial intelligence (AI) tools and emerging technologies to enhance executive productivity, streamline administrative workflows, improve communication, and drive operational efficiency.

Preferred Qualifications

• Experience in healthcare services, health technology, insurance, consulting, or a private-equity-backed environment.
• Experience supporting a board of directors and coordinating distributed leadership teams.
• Bachelor’s degree or equivalent combination of education and relevant experience.

Success Competencies

• Anticipation and initiative
• Judgment and confidentiality
• Prioritization and execution
• Executive presence and communication
• Adaptability and composure
• Stakeholder partnership
• Process improvement
• Ownership and accountability

Performance Outcomes (first 12 months)

• CEO calendar and preparation consistently reflect agreed strategic priorities, with avoidable conflicts and last-minute surprises reduced.
• Board, leadership, and client meetings are prepared accurately and on time; action items and commitments are tracked to closure.
• Travel, communications, and expense workflows are reliable, responsive, and well documented.
• CEO and designated leaders report strong confidence in responsiveness, discretion, and judgment; scope and priority conflicts are escalated early.
• At least two measurable improvements are implemented in executive-support processes or meeting effectiveness.